2-hydroxyestrone (BioDeep_00000405247)

Main id: BioDeep_00000637483

 

natural product


代谢物信息卡片


2-hydroxyestrone

化学式: C18H22O3 (286.15688620000003)
中文名称: 2-羟基雌酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC(=C(C=C34)O)O
InChI: InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

描述信息

C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents

同义名列表

2 个代谢物同义名

2-hydroxyestrone; 2-Hydroxyestrone



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Xiaoli Zhang, Na Yang, Min Wang, JiaJia Ge, Huaijun Zhu, Jun He, Weihong Ge. Establishment and validation of a sensitive LC-MS/MS method for quantification of urinary estrogens in women with gestational diabetes mellitus. Journal of pharmaceutical and biomedical analysis. 2022 Nov; 221(?):115044. doi: 10.1016/j.jpba.2022.115044. [PMID: 36126614]
  • Nhung Le, Melissa Cregger, Veronica Brown, Julio Loret de Mola, Pamela Bremer, Lyn Nguyen, Kathleen Groesch, Teresa Wilson, Paula Diaz-Sylvester, Andrea Braundmeier-Fleming. Association of microbial dynamics with urinary estrogens and estrogen metabolites in patients with endometriosis. PloS one. 2021; 16(12):e0261362. doi: 10.1371/journal.pone.0261362. [PMID: 34914785]
  • Frank Z Stanczyk. The 2-/16α-Hydroxylated Estrogen Ratio-Breast Cancer Risk Hypothesis: Insufficient Evidence for its Support. The Journal of steroid biochemistry and molecular biology. 2020 07; 201(?):105685. doi: 10.1016/j.jsbmb.2020.105685. [PMID: 32320758]
  • Vicky C Chang, Michelle Cotterchio, Beatrice A Boucher, David J A Jenkins, Lucia Mirea, Susan E McCann, Lilian U Thompson. Effect of Dietary Flaxseed Intake on Circulating Sex Hormone Levels among Postmenopausal Women: A Randomized Controlled Intervention Trial. Nutrition and cancer. 2019; 71(3):385-398. doi: 10.1080/01635581.2018.1516789. [PMID: 30375890]
  • Cynthia A Thomson, H H Sherry Chow, Betsy C Wertheim, Denise J Roe, Alison Stopeck, Gertraud Maskarinec, Maria Altbach, Pavani Chalasani, Chuan Huang, Meghan B Strom, Jean-Philippe Galons, Patricia A Thompson. A randomized, placebo-controlled trial of diindolylmethane for breast cancer biomarker modulation in patients taking tamoxifen. Breast cancer research and treatment. 2017 Aug; 165(1):97-107. doi: 10.1007/s10549-017-4292-7. [PMID: 28560655]
  • Hannah Oh, Zeina G Khodr, Mark E Sherman, Maya Palakal, Ruth M Pfeiffer, Laura Linville, Berta M Geller, Pamela M Vacek, Donald L Weaver, Rachael E Chicoine, Roni T Falk, Hisani N Horne, Daphne Papathomas, Deesha A Patel, Jackie Xiang, Xia Xu, Timothy Veenstra, Stephen M Hewitt, John A Shepherd, Louise A Brinton, Jonine D Figueroa, Gretchen L Gierach. Relation of Serum Estrogen Metabolites with Terminal Duct Lobular Unit Involution Among Women Undergoing Diagnostic Image-Guided Breast Biopsy. Hormones & cancer. 2016 12; 7(5-6):305-315. doi: 10.1007/s12672-016-0265-2. [PMID: 27138982]
  • Regina G Ziegler, Barbara J Fuhrman, Steven C Moore, Charles E Matthews. Epidemiologic studies of estrogen metabolism and breast cancer. Steroids. 2015 Jul; 99(Pt A):67-75. doi: 10.1016/j.steroids.2015.02.015. [PMID: 25725255]
  • Dina Nikitina, Marcia Llacuachaqui, Daniel Sepkovic, H Leon Bradlow, Steven A Narod, Joanne Kotsopoulos. The effect of oral 3,3'-diindolylmethane supplementation on the 2:16α-OHE ratio in BRCA1 mutation carriers. Familial cancer. 2015 Jun; 14(2):281-6. doi: 10.1007/s10689-015-9783-2. [PMID: 25613194]
  • Anushka Dikshit, Manoel Adrião Gomes Filho, Erfan Eilati, Stacey McGee, Carrie Small, Chunqi Gao, Thomas Klug, Dale Buchanan Hales. Flaxseed reduces the pro-carcinogenic micro-environment in the ovaries of normal hens by altering the PG and oestrogen pathways in a dose-dependent manner. The British journal of nutrition. 2015 May; 113(9):1384-95. doi: 10.1017/s000711451500029x. [PMID: 25850566]
  • Xiangyan Ruan, Harald Seeger, Diethelm Wallwiener, Jens Huober, Alfred O Mueck. The ratio of the estradiol metabolites 2-hydroxyestrone (2-OHE1) and 16α-hydroxyestrone (16-OHE1) may predict breast cancer risk in postmenopausal but not in premenopausal women: two case-control studies. Archives of gynecology and obstetrics. 2015 May; 291(5):1141-6. doi: 10.1007/s00404-014-3512-1. [PMID: 25318606]
  • Paulina M Merino, Daniela Martínez, German Iñiguez, Patricia Lopez, Fernando Cassorla, Francisco Perez-Bravo, Ethel Codner. Elevation of C-reactive protein during the luteal phase in healthy adolescents. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2015 Apr; 31(4):260-3. doi: 10.3109/09513590.2014.982086. [PMID: 25392126]
  • W L Gao, L S Wu, J H Zi, B Wu, Y Z Li, Y C Song, D Z Cai. Measurement of serum estrogen and estrogen metabolites in pre- and postmenopausal women with osteoarthritis using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2015 Feb; 48(2):146-53. doi: 10.1590/1414-431x20144129. [PMID: 25410577]
  • Estela Ytelina Godínez Martínez, René Santillán Ballesteros, Ana Elena Lemus Bravo, Reyna Sámano, Maricruz Tolentino Dolores, Ana Lilia Rodríguez Ventura, Ana Rosa Juárez González. [Determination of 2-hydroxyestrone /16α-hydroxyestrone ratio in urine of Mexican women as a risk indicator for breast cancer and its relationship with other risk factors]. Nutricion hospitalaria. 2014 Oct; 31(2):835-40. doi: 10.3305/nh.2015.31.2.8172. [PMID: 25617571]
  • Alan A Arslan, Karen L Koenig, Per Lenner, Yelena Afanasyeva, Roy E Shore, Yu Chen, Eva Lundin, Paolo Toniolo, Göran Hallmans, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk of breast cancer in postmenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2014 Jul; 23(7):1290-7. doi: 10.1158/1055-9965.epi-14-0009. [PMID: 24769889]
  • Nitin Telang, Gou Li, Daniel Sepkovic, H Leon Bradlow, George Y C Wong. Comparative efficacy of extracts from Lycium barbarum bark and fruit on estrogen receptor positive human mammary carcinoma MCF-7 cells. Nutrition and cancer. 2014; 66(2):278-84. doi: 10.1080/01635581.2014.864776. [PMID: 24377707]
  • Gertraud Maskarinec, Sreang Heak, Yukiko Morimoto, Laurie Custer, Adrian A Franke. The relation of urinary estrogen metabolites with mammographic densities in premenopausal women. Cancer epidemiology. 2012 Oct; 36(5):e310-6. doi: 10.1016/j.canep.2012.03.014. [PMID: 22537763]
  • Charles E Matthews, Renee T Fortner, Xia Xu, Susan E Hankinson, A Heather Eliassen, Regina G Ziegler. Association between physical activity and urinary estrogens and estrogen metabolites in premenopausal women. The Journal of clinical endocrinology and metabolism. 2012 Oct; 97(10):3724-33. doi: 10.1210/jc.2012-1732. [PMID: 22855335]
  • G Maskarinec, Y Morimoto, S Heak, M Isaki, A Steinbrecher, L Custer, A A Franke. Urinary estrogen metabolites in two soy trials with premenopausal women. European journal of clinical nutrition. 2012 Sep; 66(9):1044-9. doi: 10.1038/ejcn.2012.71. [PMID: 22713773]
  • N T Telang, G Li, D W Sepkovic, H L Bradlow, G Y C Wong. Anti-proliferative effects of Chinese herb Cornus officinalis in a cell culture model for estrogen receptor-positive clinical breast cancer. Molecular medicine reports. 2012 01; 5(1):22-8. doi: 10.3892/mmr.2011.617. [PMID: 21971582]
  • Yukiko Morimoto, Shannon M Conroy, Ian S Pagano, Marissa Isaki, Adrian A Franke, Frank J Nordt, Gertraud Maskarinec. Urinary estrogen metabolites during a randomized soy trial. Nutrition and cancer. 2012; 64(2):307-14. doi: 10.1080/01635581.2012.648819. [PMID: 22293063]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Nadia Obi, Alina Vrieling, Judith Heinz, Jenny Chang-Claude. Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer?. International journal of women's health. 2011 Feb; 3(?):37-51. doi: 10.2147/ijwh.s7595. [PMID: 21339936]
  • Lulu Fu, Hong Xu. A preliminary study of the effectiveness of chinese therapeutic food on regulating female reproductive hormones. Integrative medicine insights. 2011; 6(?):7-12. doi: 10.4137/imi.s5782. [PMID: 21614163]
  • Maggie Laidlaw, Carla A Cockerline, Daniel W Sepkovic. Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial. Breast cancer : basic and clinical research. 2010 Dec; 4(?):85-95. doi: 10.4137/bcbcr.s6505. [PMID: 21234288]
  • W Gao, C Zeng, D Cai, B Liu, Y Li, X Wen, Y Chen. Serum concentrations of selected endogenous estrogen and estrogen metabolites in pre- and post-menopausal Chinese women with osteoarthritis. Journal of endocrinological investigation. 2010 Oct; 33(9):644-9. doi: 10.1007/bf03346664. [PMID: 20339312]
  • Emanuela Taioli, Annie Im, Xia Xu, Timothy D Veenstra, Gretchen Ahrendt, Seymour Garte. Comparison of estrogens and estrogen metabolites in human breast tissue and urine. Reproductive biology and endocrinology : RB&E. 2010 Aug; 8(?):93. doi: 10.1186/1477-7827-8-93. [PMID: 20678202]
  • R G Ziegler, J M Faupel-Badger, L Y Sue, B J Fuhrman, R T Falk, J Boyd-Morin, M K Henderson, R N Hoover, T D Veenstra, L K Keefer, X Xu. A new approach to measuring estrogen exposure and metabolism in epidemiologic studies. The Journal of steroid biochemistry and molecular biology. 2010 Aug; 121(3-5):538-45. doi: 10.1016/j.jsbmb.2010.03.068. [PMID: 20382222]
  • Susan R Sturgeon, Stella L Volpe, Elaine Puleo, Elizabeth R Bertone-Johnson, Joanna Heersink, Sara Sabelawski, Kristina Wahala, Carol Bigelow, Mindy S Kurzer. Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women. Nutrition and cancer. 2010; 62(2):175-80. doi: 10.1080/01635580903305342. [PMID: 20099191]
  • Jessica M Faupel-Badger, Barbara J Fuhrman, Xia Xu, Roni T Falk, Larry K Keefer, Timothy D Veenstra, Robert N Hoover, Regina G Ziegler. Comparison of liquid chromatography-tandem mass spectrometry, RIA, and ELISA methods for measurement of urinary estrogens. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2010 Jan; 19(1):292-300. doi: 10.1158/1055-9965.epi-09-0643. [PMID: 20056650]
  • Maddalena Barba, Li Yang, Holger J Schünemann, Francesca Sperati, Sara Grioni, Saverio Stranges, Kim C Westerlind, Giovanni Blandino, Michele Gallucci, Rossella Lauria, Luca Malorni, Paola Muti. Urinary estrogen metabolites and prostate cancer: a case-control study and meta-analysis. Journal of experimental & clinical cancer research : CR. 2009 Oct; 28(?):135. doi: 10.1186/1756-9966-28-135. [PMID: 19814782]
  • Annie Im, Victor G Vogel, Gretchen Ahrendt, Stacy Lloyd, Camille Ragin, Seymour Garte, Emanuela Taioli. Urinary estrogen metabolites in women at high risk for breast cancer. Carcinogenesis. 2009 Sep; 30(9):1532-5. doi: 10.1093/carcin/bgp139. [PMID: 19502596]
  • Alan A Arslan, Roy E Shore, Yelena Afanasyeva, Karen L Koenig, Paolo Toniolo, Anne Zeleniuch-Jacquotte. Circulating estrogen metabolites and risk for breast cancer in premenopausal women. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2009 Aug; 18(8):2273-9. doi: 10.1158/1055-9965.epi-09-0312. [PMID: 19661086]
  • Go Li, Daniel W Sepkovic, H Leon Bradlow, Nitin T Telang, George Y C Wong. Lycium barbarum inhibits growth of estrogen receptor positive human breast cancer cells by favorably altering estradiol metabolism. Nutrition and cancer. 2009; 61(3):408-14. doi: 10.1080/01635580802585952. [PMID: 19373615]
  • Roni T Falk, Xia Xu, Larry Keefer, Timothy D Veenstra, Regina G Ziegler. A liquid chromatography-mass spectrometry method for the simultaneous measurement of 15 urinary estrogens and estrogen metabolites: assay reproducibility and interindividual variability. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Dec; 17(12):3411-8. doi: 10.1158/1055-9965.epi-08-0355. [PMID: 19064556]
  • Charlotte Atkinson, Katherine M Newton, Frank Z Stanczyk, Kim C Westerlind, Lin Li, Johanna W Lampe. Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States. Cancer causes & control : CCC. 2008 Dec; 19(10):1085-93. doi: 10.1007/s10552-008-9172-3. [PMID: 18478336]
  • Mylène Aubertin-Leheudre, Sherwood Gorbach, Margo Woods, Johanna T Dwyer, Barry Goldin, Herman Adlercreutz. Fat/fiber intakes and sex hormones in healthy premenopausal women in USA. The Journal of steroid biochemistry and molecular biology. 2008 Nov; 112(1-3):32-9. doi: 10.1016/j.jsbmb.2008.08.002. [PMID: 18761407]
  • MaryFran R Sowers, John Randolph, Mary Jannausch, Bill Lasley, Elizabeth Jackson, Daniel McConnell. Levels of sex steroid and cardiovascular disease measures in premenopausal and hormone-treated women at midlife: implications for the "timing hypothesis". Archives of internal medicine. 2008 Oct; 168(19):2146-53. doi: 10.1001/archinte.168.19.2146. [PMID: 18955645]
  • Latanya M Scott, Xia Xu, Timothy D Veenstra, Janet A Tooze, Charles E Wood, Thomas C Register, Nancy D Kock, J Mark Cline. Past oral contraceptive use and current dietary soy isoflavones influence estrogen metabolism in postmenopausal monkeys (Macaca fascicularis). Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2008 Oct; 17(10):2594-602. doi: 10.1158/1055-9965.epi-08-0278. [PMID: 18843000]
  • MaryFran Sowers, Daniel McConnell, Mary L Jannausch, John F Randolph, Robert Brook, Ellen B Gold, Sybil Crawford, Bill Lasley. Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress. Clinical endocrinology. 2008 May; 68(5):806-13. doi: 10.1111/j.1365-2265.2007.03108.x. [PMID: 17980014]
  • Sarah M Mense, Tom K Hei, Ramesh K Ganju, Hari K Bhat. Phytoestrogens and breast cancer prevention: possible mechanisms of action. Environmental health perspectives. 2008 Apr; 116(4):426-33. doi: 10.1289/ehp.10538. [PMID: 18414622]
  • Melissa J Wentz, Shao-Qing Shi, Leili Shi, Salama A Salama, Hassan M Harirah, Hala Fouad, Robert E Garfield, Ayman Al-Hendy. Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats. Reproduction (Cambridge, England). 2007 Dec; 134(6):831-9. doi: 10.1530/rep-07-0245. [PMID: 18042640]
  • Masatoki Katayama, Kiyoshi Takamatsu, Satoru Kaneko, Keisuke Miyaji, Hiromichi Ishikawa, Yoshifumi Matsuda. HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector. Journal of separation science. 2007 Sep; 30(14):2279-85. doi: 10.1002/jssc.200700096. [PMID: 17668912]
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